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    All listings in Annapolis

    Search yacht rentals in Annapolis, Maryland.

    5.0
    (136 Reviews)

    Page 1 of 1 • 23 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    Private Yacht Charter: On 40ft Regal Commodore
    Events in Selby-on-the-Bay · 10 guests

    Private Yacht Charter: On 40ft Regal Commodore

    5.0
    $300/hour
    JEHM of the SEA 2014 CATALINA 445 Sailboat for Amazing Day in Chesapeake Bay!
    Sailing in Annapolis · 12 guests

    JEHM of the SEA 2014 CATALINA 445 Sailboat for Amazing Day in Chesapeake Bay!

    5.0
    $250+/hour
    Luxury SeaRay Yacht with Captain | Explore the Annapolis Waterways
    Events in Annapolis · 8 guests

    Luxury SeaRay Yacht with Captain | Explore the Annapolis Waterways

    5.0
    $250/hour
    50ft Catamaran Charter with Water Toys - Annapolis, MD
    Sailing in Annapolis · 12 guests

    50ft Catamaran Charter with Water Toys - Annapolis, MD

    5.0
    $325/hour
    SWEET & SALTY FOUNTAINE PAJOT HELIA 44 CATAMARAN
    Sailing in Annapolis · 12 guests

    SWEET & SALTY FOUNTAINE PAJOT HELIA 44 CATAMARAN

    5.0
    $400+/hour
    Luxurious 51’ SeaRay Flybridge Yacht With Twin 600 Hp Cummins Engine
    Events in Deale · 10 guests

    Luxurious 51’ SeaRay Flybridge Yacht With Twin 600 Hp Cummins Engine

    5.0
    $500/hour
    Captain Bill invites you to find your Sailing Dream on Chesapeake Bay.
    Sailing in Mayo · 6 guests

    Captain Bill invites you to find your Sailing Dream on Chesapeake Bay.

    5.0
    $175+/hour
    STARZ -Lagoon 42 Catamaran in Chesapeake Bay
    Sailing in Annapolis · 13 guests

    STARZ -Lagoon 42 Catamaran in Chesapeake Bay

    5.0
    $400+/hour
    Charter 44' Orana Cruising Catamaran In Deale, Maryland
    Sailing in Deale · 10 guests

    Charter 44' Orana Cruising Catamaran In Deale, Maryland

    5.0
    $250+/hour
    Instant Book
    43ft Cruiser Express Yacht for Daily Charter
    Events in Selby-on-the-Bay · 8 guests

    43ft Cruiser Express Yacht for Daily Charter

    5.0
    $400/hour
    SLOWDOWN - DUFOUR 430
    Sailing in Annapolis · 12 guests

    SLOWDOWN - DUFOUR 430

    New
    $250+/hour
    Charter 42' Lagoon Catamaran in Annapolis, MD
    Sailing in Edgewater · 12 guests

    Charter 42' Lagoon Catamaran in Annapolis, MD

    5.0
    $425/hour
    50′ VIKING - Your Chartered Experience Awaits!
    Events in Annapolis · 12 guests

    50′ VIKING - Your Chartered Experience Awaits!

    New
    $841+/hour
    Relaxing Excitement of the Chesapeake Bay and tributaries on our Yacht
    Events in Annapolis · 6 guests

    Relaxing Excitement of the Chesapeake Bay and tributaries on our Yacht

    New
    $300/hour
    Enjoy a Luxurious Boat Cruise on the Chesapeake Bay, Maryland
    Events in North Beach · 8 guests

    Enjoy a Luxurious Boat Cruise on the Chesapeake Bay, Maryland

    5.0
    $400/hour
    Enjoy the best views of Annapolis, MD aboard the Island Princess
    Events in Annapolis · 128 guests

    Enjoy the best views of Annapolis, MD aboard the Island Princess

    New
    $600+/hour
    Sail in Style Aboard the 2024 Seawind 1160 Lite – Your Perfect Charter Escape
    Sailing in Annapolis · 13 guests

    Sail in Style Aboard the 2024 Seawind 1160 Lite – Your Perfect Charter Escape

    New
    $350+/hour
    DOS MILAGROS Beneteau Oceanis 45 Sailing Yacht in Chesapeake Bay!
    Sailing in Annapolis · 10 guests

    DOS MILAGROS Beneteau Oceanis 45 Sailing Yacht in Chesapeake Bay!

    New
    $232+/hour
    46′ CARMEN | Take Everybody With You! | Captain Included
    Events in Annapolis · 30 guests

    46′ CARMEN | Take Everybody With You! | Captain Included

    New
    $670+/hour
    Maxum 30ft Yacht! Escape for a day on the Chesapeake
    Events in Selby-on-the-Bay · 6 guests

    Maxum 30ft Yacht! Escape for a day on the Chesapeake

    New
    $350/hour
    Romantic Sunset Champagne Cruise on the Chesapeake Bay - 2 Hours
    Sailing in Saint Michaels · 6 guests

    Romantic Sunset Champagne Cruise on the Chesapeake Bay - 2 Hours

    New
    $400/hour
    New Yacht Charter Bali 5.4 Sailing Catamaran in Annapolis Maryland
    Sailing in Annapolis · 13 guests

    New Yacht Charter Bali 5.4 Sailing Catamaran in Annapolis Maryland

    New
    $1,100/hour
    Discover the Spirit of the Chesapeake Bay with our Nautical-Themed Photography
    Events in Annapolis · 6 guests

    Discover the Spirit of the Chesapeake Bay with our Nautical-Themed Photography

    New
    Snoozed - Active 04 Jul 2025

    Top Destinations Nearby

    Motor Yacht Reviews in Annapolis

    1. CB

      Caroline

      Private Yacht Charter: On 40ft Regal Commodore

      Captain Dennis is absolutely fantastic. Great communication, fabulous boat and amenities, and a wonderful captain. Would highly recommend!

    2. MR

      Matt

      STARZ -Lagoon 42 Catamaran in Chesapeake Bay

      Great experience and our family and friends had a wonderful time. Clean boat and fun crew to help us celebrate a special occasion. Highly recommend!

    3. hg

      hunter

      Captain Bill invites you to find your Sailing Dream on Chesapeake Bay.

      we did our engagement pictures on the boat & everything was great! Bill was super cooperative & made sure we got all of the best spots for pictures! highly recommend!

    4. TP

      Tarak

      Luxury SeaRay Yacht with Captain | Explore the Annapolis Waterways

      Captain McCoy was the best. Responded to all my messages right away and provided above and beyond service. Great boat and great captain! Recommend to everyone!

    5. CE

      Clifford

      SWEET & SALTY FOUNTAINE PAJOT HELIA 44 CATAMARAN

      Sarah was helpful in lining me up for a sail boat for Mothers Day and in recommending a captain and in adjusting time to meet our needs.

    6. EB

      Ernest

      Private Yacht Charter: On 40ft Regal Commodore

      GREAT experience!!! Captain Dennis was terrific. He was professional, yet fun & extremely well prepared. The yacht was clean & well maintained with all the amenities that we could ask for. Our only regret is that we did not book a longer cruise on Seas the Day.

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